ArticleAngewandte Chemie (International ed. in English)2022
Photocatalytic gem-Difluoroolefination Reactions by a Formal C-C Coupling/Defluorination Reaction with Diazoacetates.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Direct Synthesis of Bicyclo[1.1.1]pentanes by Sequential C═C, C-C Functionalization Reactions.Journal of the American Chemical Society · 2025Article
- Redox-neutral photocatalytic cleavage andScience advances · 2025Article
- A toolbox approach to revealing a series of naphthocarbazoles to showcase photocatalytic reductive syntheses.Chemical science · 2024Article
- Reductive Cyclopropanation through Bismuth Photocatalysis.Journal of the American Chemical Society · 2024Article
- Visible Light-Induced Reactions of Diazo Compounds and Their Precursors.Chemical reviews · 2024Review
- Photochemical synthesis of 1,2,4-triazolesChemical science · 2022Article
- Photocatalytic C(spChemical science · 2022Review
- Photocatalytic gem-Difluoroolefination Reactions by a Formal C-C Coupling/Defluorination Reaction with Diazoacetates.Angewandte Chemie (International ed. in English) · 2022Article
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3 authors.
Funding
Abstract
The photolysis of diazoalkanes to conduct singlet carbene transfer reactions of colored diazoalkanes has recently attracted significant interest in organic synthesis. Herein, we describe a photocatalytic approach that allows the access of triplet carbene intermediates via energy transfer to conduct highly efficient gem-difluoroolefination reactions with α-trifluoromethyl styrenes. The use of a tertiary amines proved pivotal to unlock this unusual reaction pathway and to prevent undesired cyclopropanation pathways. The amine further facilitates the ultimate abstraction of fluoride to yield gem-difluoroolefins (43 examples, up to 88 % yield), which is supported by experimental and theoretical mechanistic studies. We explored this synthesis method with a broad substrate scope, ranging from simple olefins and heterocyclic olefins towards the decoration of pharmaceutically relevant building blocks.
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